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Niccolo Machiavelli (1469-1527) has long been recognized as a realist who helped move political philosophy into the modern era. Among his well-known assertions: When a ruler needs to choose between instilling fear or inspiring love within their realm, better to err on the side of fear. A lesser-known theorist, Christine de Pizan (1364-1431), made the opposite assertion: When faced with such a choice, a ruler should err on the side of love. This paper looks at the assumptions behind each position and its implications for political life today. For Machiavelli, political life is a transactional, strategic enterprise, characterized by the need to exert authority, preempt dissent, and subdue would-be rivals. For Pizan, political life is relational and cooperative. It is characterized by a will to pursue the common good and reconcile, rather than suppress, dissenters. It isn’t difficult to draw parallels between Machiavellian and Pizanesque approaches to governance in today’s world. Around the globe, we see authoritarian models of leadership under which members of society begrudgingly cower and comply, but are unable to fully engage and participate. Pizan’s model, while perhaps too idealistic, allows the possibility for members of society to be politically engaged and more fully invested in governance. Drawing on feminist theories of care and altruism, this paper explores what it would mean to follow Pizan’s counsel and “err on the side of love” in a political context.